


Speed Date #8

by orphan_account



Category: Supernatural
Genre: F/M, Trans Dean, Transmisogyny, trans woman Dean
Language: English
Status: Completed
Published: 2015-04-09
Updated: 2015-04-09
Packaged: 2018-03-22 00:10:20
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,733
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3708149
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: <blockquote class="userstuff">
              <p>Gilda begs Dean to join her for a speed dating session; she doesn't have a ride, and it'll be good for Dean. Reluctant but unwilling to hurt her friend's feelings and be overly pessimistic, Dean agrees to go.</p>
            </blockquote>





	Speed Date #8

Dean shoves more fries into her mouth as Gilda stares her down. Maybe if she just doesn’t respond, Gilda will take it back and they can pretend this exchange never happened.

Luck isn’t on Dean’s side today.

“Dean.” Gilda does the thing where her facial features don’t change, but her tone gets dangerously low. Low for her, anyway. “It’ll be good for you.”

Meeting strangers is never good for Dean, but that’d sound too bitter to say out loud. “I’m not interested.”

“Please? I’d ask Charlie, but her and Dorothy just went steady.”

“Absolutely no one says that anymore.”

Gilda frowns at her. “I don’t care. It’s what happened.” Her face morphs into worry. “I can’t go by myself. You know I can’t drive and how expensive taxis are here.”

“Gilda. It’d be one thing to be your ride, but you asked me to participate.”

“Because you haven’t been on a date in forever.”

Dean acutely feels the need to pinch the bridge of her nose like Sam used to do before he started getting regular massages and actually got a headache prescription. “Gilda, have you considered I don’t want to date? Maybe, just maybe, that’s why I’m not.”

“But that’s not why. Charlie and I talk, you know.”

“Then I need to add Charlie to my hit list. And you know why I’m not going.”

“It’s an LGBT friendly speed date, Dean!”

Dean barely holds back her eye roll. That means absolutely nothing to her, and it’s a true testament to Gilda’s obliviousness that she thinks it does. More fries get crammed into Dean’s mouth.

Gilda puts her hand on Dean’s. “I know you aren’t big on the community, but come on. You’re more likely to find someone here, right?”

She seems so earnest, and Dean doesn’t have the heart to be the pessimistic asshole. Gilda is right, though Dean knows her chances are only fractionally better; she’s still considered a freak by what Dean would bet is over half, maybe two-thirds, of the so called community. She swallows her fries and accepts she’s in for a shitty night in her near future. “Fine.”

“Really?!” Her whole face lights up.

Dean nods. “Really.”

Gilda bursts out of her seat and plants a big kiss on Dean’s cheek before heading to find her phone to sign Dean up. Dean hopes Gilda doesn’t trip, she’s so excited.

-

Dissatisfied eyes look Dean over on the 20th, the day of the speed date. Dean lifts an eyebrow at Gilda.

“You’re going on dates, Dean. You couldn’t have...dressed up a little?”

Dean thinks her jeans and flannel are just fine. She’d look stupid in a “little black dress” outfit like Gilda’s wearing, and why would she even dress up? None of the people are ones Dean’s trying to impress, and the establishment they’re going to isn’t particularly fancy. Her outfit is fine. Dean says as much.

Gilda sighs in response. “You’re hopeless.”

“Think of it as I’m giving an honest first impression. When was the last time you saw me in anything that wasn’t flannel and jeans?”

“Besides undies or LARP gear? Never.”

“So what made you think I’d wear anything different tonight?”

“Uh, it’s a date? I’ve never seen you before one of those; I’d have assumed you’d have some class.”

Dean pulls open the door to Gilda and Charlie’s apartment. “Well, I don’t.”

“It’s a tragedy.”

Eyes roll as Gilda steps past her to get out of the door. Dean follows, the two of them walking down the stairs to get to the parking lot. They climb into Dean’s car, and Dean drives them out of town to the bar the speed date is. The drive is spent with Gilda nervously chatting away while Dean tries her best not to upset her further.

Gilda takes care of guiding Dean to the bar and getting them through the door. The front organizer asks for their IDs to check they’re signed up, and when she’s satisfied they get stickers to pin onto their shirts. Pink for girl, and another sticker for orientation. A pink circle with a cartoony skirt on it gets patted onto Gilda’s chest, and Dean sticks one with a purple “2” on. Apparently there’s nothing “cute” for bisexual.

They mill about for a few minutes as everyone waits for 8:30 to roll around. Dean orders herself a drink and nachos; she’s probably going to need something to distract herself from whomever she gets stuck with. Gilda gives a disapproving look, but Dean ignores it. She’s not the one hoping to score tonight.

The main event organizer calls attention the second the clock behind the bartender strikes the half hour. He explains that lesbians will sit at tables to the left, gay men will be situated to the right, and bisexuals will sit in the center while shuffling through the sections. People sitting facing the entrance will remain seated throughout all the dates. Dean rolls her eyes as the organizer keeps going; everyone gets it, if the bored looks are anything to go by.

When they are finally released to find their first table, marked with their names, Dean rolls her shoulders. A glance at Gilda shows she’s smiling, her face light up like a Christmas tree. Dean turns back to look in front of herself. Her table is in the middle of the starting bisexual section. Dean drops her nachos onto the table and pulls out her chair. She plops into it, pulling from her beer while she waits for her date – Ashley, the name plate across the table reads – to make their way over.

A pretty woman seats herself across from Dean; she’s got the sexy bed-head look going for her, and her dress fits like a glove. Dean finds her interest piqued despite herself. A smile grows on her face, though she doesn’t let her hopes go up. That proves to be for the best as Ashley takes one look at Dean’s chest and scowls. Her whole face transforms from attractive to monstrous.

“My first date is you?”

Dean’s hackles shoot up. “My first date is you? I think I’m the one who’s gotten the short end of the stick here.”

“I can’t believe my first date is with a tranny.” Ashley’s lips curl disdainfully. 

Dean wants to punch Ashley in her goddamn face. The only thing stopping her is thoughts of Gilda; it’s her night, and Dean knew this was going to happen. She knew it would.

The rest of the so-called date is thankfully spent in silence, Ashley doing a woe-is-me party of facial expressions and Dean aggressively eating her nachos.

Dean washes down her nachos with a swig of beer as her second date starts. This one is a twig of a man, and he’s nervous. But he smiles nicely at her, so Dean puts down her bottle.

“The name’s Dean.”

“Dave.”

The two of them don’t have much to talk about. Dave’s practically a baby, he’s so young, and Dean isn’t into much of what Dave is. Dave’s all social media whereas Dean...isn’t. Their date is mostly awkward.

Date number three is Steven, a meathead Dean really wishes she’d had the luxury to have never met. He’d been insulted seeing Dean was his date, and things had rapidly escalated; Dean had to punch him he was so horrible, consequences be damned. Organizers had to come separate them. Dave was sent home, permanently banned from future events, and Dean got a warning after what caused the fight came to light. When the organizer leaves to do damage control, Dean lets her eye roll go. She’s definitely not coming to any more of these.

Dean refuses to meet Gilda’s eyes across the room, and she leaves her table to buy another beer and nachos. She hates this; seven more dates is seven too many. Maybe she could just leave and sit in the Impala. It’d infinitely be a better use of her time.

A touch on her shoulder startles her. Dean whips around, ready to scowl at whoever it is, but it’s just Gilda. She looks worried.

“Dean, are you okay?”

Dean plasters a cocky smile onto her face. “Of course I am. You probably missed the excellent hook I got in.”

“Dean.”

The smile falls off her face. “Gilda, I don’t know what the fuck else you were expecting with me here. Next to no one wants to date someone like me. I’m not the hot chick everybody falls over, in case you haven’t noticed.”

“You’re plenty hot.” It’s a weak attempt at comfort, and Dean thinks Gilda is finally starting to get the scope of things. 

“Go finish your date, Gilda.”

She shakes her head. “We can go home now.”

“Nah. You’ve got another seven dates to get through, and me? I’ve got nachos to stuff myself with.”

“Dean, I'm–”

“Don’t, okay? I don’t wanna talk about it. It happened, I knew it would, it’s over with. Go back to your date.” Gilda doesn’t move. “For me? I’d hate for the both of us to have flushed fifty bucks down the toilet.”

Gilda’s face is a mess, regret and sadness mixed with a smidgeon of irritation. But she listens to Dean, and away she goes to find her next date. The sound of the bell echoes as Gilda sits down. Dean throws her head back, beer flowing. 

Dean sits at the bar for this round. Her date’ll figure it out, who was supposed to be sitting across from them. Dean doesn’t give a shit, and she polishes off her nachos while talking with the bartender. His name’s Benny, and he’s alright. He doesn’t like being on shift for the speed dates; mostly his shift consists of standing and looking pretty because everyone’s too busy to drink. Dean laughs at that and salutes Benny with her beer. She’s happy to bring some entertainment to his night. 

The sound of the bell for the end of the date draws an irritated scowl from Dean. Benny is much better company than all of her dates so far, and she really doesn’t want to jump back in now that she's has some cool down time. Benny lifts an eyebrow at her.

“Darlin’, I think that means you’ve got a date.”

“I already missed one. What’s six more?” Dean smiles lasciviously at him.

Benny rolls his eyes. “Ain’t no one gonna try anything again after seeing you in action. You can catalogue ‘em all and came back, give me a rundown.” 

“You live for others’ pain,” accuses Dean.

“Ain’t nothin’ better.”

Dean pulls her beer off the table and climbs off her stool. “I expect my next one on the house.”

“Only if you tough out all six dates.”

“I expect more than one beer, then.” 

Benny watches her make her way to her table, and Dean sticks her tongue out before turning to her date and sitting down. Her date’s eyes trail over the stickers on her chest before settling back on her face. Dean grinds her teeth at quick flash of discomfort from him.

“The name’s Dean.”

“Victor. Nice handling of your last date. Your form could use work, but it was nice.”

Dean narrows her eyes. “Nothing’s wrong with my fighting form, mister. In case you’re blind, I was winning.”

“Because he had no form whatsoever.”

“You’re not very flattering for a date.”

“You’re not very date-like, so. Flannel and jeans, really?”

“Comfort, dude. No way I’m dressing up for losers.”

Victor cocks an eyebrow. “Mighty high opinion of yourself.”

“Because I’m worth it.” Dean smirks.

Victor snorts before sipping at his drink. “If you say so.” He takes another sip. “So, why are you even here if this is you slumming it?”

“Dragged with a friend.”

“Who?”

Dean looks around the bar; Gilda’s at a far table now, and Dean points once she locates her. Victor follows her arm. 

“Your friend actually looks like she’s here to date.”

“Whatever. Why are you doing the speed date gig?”

Victor sighs. “My coworker invited me. I haven’t had the time to date recently.”

“Is your coworker here?”

Dean’s gaze follows Victor’s to a table closer to the right side of the bar. One of the men at the table Victor’s eyes stop at is engaging in telling what looks like a ridiculous story the way his arms are flailing in excitement while the second looks bored out of his mind. Dean snorts into her beer at the sight. 

“Which one do you work with?”

“The stupid one.”

“Is he usually so oblivious to people?”

Victor sighs deeply, and Dean laughs. 

“Sorry, dude.”

“You learn to tune him out after a while.”

Dean nods at that, and the two of them ease into a silence. Victor finishes off his beer while Dean itches for the date to be over. It’s been an okay enough time for what it is, but Victor obviously isn’t into her and is just trying to be polite. Dean takes a swig of beer as Victor picks at his bottle. 

Hearing the bell is a relief for both of them. Dean can see Victor’s shoulders relax minutely before he leaves the table. She tries to shrug it off as her next date fills the empty seat across from her. Her new date is an older woman, hair fixed in what looks like an expensive up-do. Dean puts on a charming smile in hopes to stave off the worst. 

“You can call me Miranda.” Her eyes look Dean up and down, her lips curling into a very interested smile. “What can I call you?”

“Keep looking at me like that, and you can call me almost anything you want.”

Miranda laughs. “I’ll keep that in mind. But tell me your name.”

“Dean.”

“Dean? I would have expected something prettier for a woman like you.”

Dean laughs; she can’t help it. A woman like her? Dean fits just fine. A prettier name would neither match her nor be something she could respond to. “I like Dean.”

“Well, I suppose that’s all that truly matters. God, look at you.”

Dean shifts in her seat. Miranda’s gaze is heavy. 

“You’ve got really pretty lips, Dean. Very kissable. Do you think that’s against the date rules?”

Dean licks her lips and smiles. “Might be breaking some unwritten public decency rules, but I’m game.” 

Miranda’s foot, now without a black heel, presses against the outside of Dean’s thigh. Her hand curls on top of Dean’s, and Dean turns it so her fingers interlace with Miranda’s. Miranda bites her lip. 

“Honestly, I think I want to take you home. Your thigh feels really firm; I can’t imagine what everything else feels like under all your layers.”

“I can assure you my boobs are the soft kind.”

Miranda laughs again. “Those are the best kind. Tell me: are they sensitive? Can I get you going just playing with them alone?” 

All Dean can get do is suck in a breath before Miranda continues.

“Bet I wouldn’t even need to touch you anywhere else to get off, just play with your breasts.” Miranda smirks while Dean adjusts her legs. “Like that, do you? I think I’d tease you, draw it out until you beg me to do something – anything – to get you off.”

Dean lets her grip get tight on Miranda’s hand. “What makes you think I’d just let you do that to me?”

“Oh, Dean.” Miranda moves her foot above Dean’s crotch and waits for Dean to nod. She rubs against the denim. “I think this is why you’d just let me do that to you. Your downstairs is very interested. How’d you react if I put my mouth there, hm? Are you loud, Dean? Or are you a quiet girl, have your mouth hanging open with no sound coming out? Either way, I think I’d like to. Just suck you off until you’re close and stop. Climb back up and kiss you for a bit. Would you be able to kiss me back or would you be too breathless, Dean?”

Dean groans before she answers. “I’d kiss you back.”

“Mm. And how desperate would you be for me to finish what I started?”

“How ever desperate you want me to be.”

“So sweet of you. What do you say we leave and I make good on my word?”

Dean’s grip tightens to what she thinks might be painful, but Miranda gives no indication she even notices. It's been a long time since she's been with someone. “I would love to. But I can’t. I came with someone. She won’t have a ride back home.” Dean shifts, adjusting her legs. “I really would love to.”

Miranda pouts, and that’s an expression Dean’s never seen on someone her age. It’s especially weird coming from Miranda who’s been nothing but domineering and sexual. 

“We could raincheck?”

Miranda pulls Dean’s hand to her face to kiss it. “I suppose we’ll have to. Hope you don’t get snatched up with one of your other dates.”

“No way. I think I’ve got more to be afraid of. You’re charming.”

Miranda quirks her lips. “Or too sexually aggressive, as has been said.”

“Well, maybe a little for most people.”

“And you definitely aren’t most people, Dean.”

“You bet I’m not.”

Miranda lets their hands drop to the table. “It’s too bad these dates aren’t longer. We could’ve at least had some fun in the bathroom.”

“A damn shame.”

“I know.” Miranda turns her attention to the card all participants were given before they started the rounds. “But we have our raincheck.” 

She proceeds to fill out the necessary details saying she would like Dean’s contact information, and Dean does the same with her card. She’s tempted to just ask for Miranda’s number then and there, but Miranda shakes her head. 

“The both of us could find a partner we like better. It’s best to just get each other’s numbers after this whole thing. We can exchange before we leave.”

Dean can’t find an argument for that. 

Both of them jump a bit at the sound of the bell, its jarring intensity breaking their silence. Miranda kisses Dean’s hand again, and she runs her fingers along Dean’s hair and the tip of her ear as she leaves. Dean sadly watches her go.

The next person to sit across from Dean is a man who just screams gross. His hair’s slicked back with way too much gel, and it looks like a leer naturally sits on his face. Dean crinkles her nose as he opens his mouth after checking out her stickers. 

“So you’re...one of those women with a dick, right?”

Dean wants to gag. “And you’re one of those disgusting guys who ask after women’s genitals.”

“I think I deserve to know if I’m supposed to think of you as my date.”

“I think it’s none of your damn business, and I’m gonna punch you if the damn face if you say anything else to me.” The man opens his mouth. “ _Anything_ to me.”

Smartly, the man closes his mouth. Dean turns her attention to the bar, trying to see if Benny’s unoccupied. He’s cleaning shot glasses, and Dean sighs. She chugs some more of her beer. The next thing she knows, it’s finished. 

Hearing the bell is a God send. If Dean were the religious type, she thinks she’d send up a prayer in thanks. As it is, she mutters a fucking finally under her breath and hopes her next date is decent. 

Date number seven (or eight, if Dean counts her round with Benny and the bar) has messy hair and the ugliest overcoat Dean’s ever seen. As he sits down, Dean swallows as his eyes meet hers. Dude’s got intense as fuck eyes. 

He gives Dean a teeny smile. “Hello.”

“Hey.”

“I’m Cas.”

Dean nods. “Dean.”

“Nice to meet you.”

“Are you always this polite?”

Cas blinks. “It’s my understanding that you’re supposed to be polite on the first date.”

“Well, not this one. Talk to me like you talk usually, dude.”

“My usual manner of speech isn’t much different, Dean. I’m so sorry too disappoint.” 

He doesn’t sound sorry at all, and it causes Dean to smile. “You should make it up to me.”

“And how would I do that?” He lifts an eyebrow.

“You could buy me another drink?”

Cas looks at Dean’s empty bottle. “Are you already so tired of my presence that you’re resorting to drinking?”

“Drinking is what you do on dates, too. We’re in a bar.”

“Isn’t a man buying a woman drinks in a bar usually a sign he’s trying to get sex from her?”

Dean lets out a small laugh, both at Cas’s statement and his phrasing. “Are you saying you don’t want in my pants?”

“I’m not interested in sex on the first date, no.”

“No? I put out on the first date, Cas.”

Cas blushes, and his eyes go to Dean’s mouth. Dean lets her tongue swipe her lips. Flushed looks good on Cas, and Dean thinks she wants to keep it on him.

“I’m told I give great head, if that’s what you’re thinking about.”

His face gets even redder, but his speech is just as clear as when they started talking. “Are you this forward with everyone?”

“Only with the cute ones.”

“And how many cutes ones have there been tonight?”

“Jealous?”

“Wondering if I should allow my hopes up.”

Dean reaches her hand out to Cas, and she closes her fingers around his hand when he gives it to her. “It’s just been you and Miranda. I dunno if you ran into her tonight.”

“No, I haven’t.”

“Well, uh, yeah. Just you two.”

“Very eloquent, Dean,” teases Cas.

“Shut up.” Dean stares at their joined hands. “So, date stuff.”

“Yes. That is what we are doing.”

“No, I mean– I don’t know where I was going with that.”

“Mm. What do you do for a living?”

Dean brings her gaze back up to Cas’s face. “Mechanic. You?”

“I’m a contractor.” 

“What type?”

“Military.”

“Ooooo, dangerous.”

Cas squeezes Dean’s hand. “I don’t do dangerous anymore. That’s why I’m a contractor.” 

“Mm. What exactly do you do as a contractor?”

“Help with training, look over weaponry.”

Dean whistles. “Fun stuff there.”

“Not really.”

“I wasn’t being literal, Cas.”

“Oh.”

“Yeah.”

The two of them sit in silence for a while. Dean adjusts herself on her seat and wipes her free hand on her jeans. Cas smiles softly at her the whole while. 

“So, any disaster dates tonight?”

Cas shakes his head. “I was fortunate. I’m sorry you haven’t had the most pleasant partners tonight.”

“Wha– oh man, did you see the fight?”

“I think everyone did, Dean.”

“Well, I was awesome, wasn’t I?”

“Yes, you were. A regular woman in her own shining armor.”

Dean scrunches her nose. “Dude, I don’t know what you’re getting at. I just decked a douchebag.”

“It’s something my mother used to tell my sisters.”

“Good for them, I guess. How many do you have?”

“Five. Do you have any siblings?”

“A little brother.”

“Mm–”

The sound of the bell interrupts whatever else Cas was going to say. Dean scowls in the direction of the organizer, and Cas squeezes her hand. 

“I guess this is goodbye for now.”

“Dude, no. I’ll catch up to you after the rest of these? There’s only two more, right?”

Cas nods, his smile blinding. “That works for me, Dean.”

“Cool.”

Dean is reluctant to let go of Cas’s hand, and it’s only when Cas pulls that she lets him leave. Cas laughs softly at her. Dean pretends to not hear it as her eyes follow Cas to his next table. She whistles at Cas’s next date; his date is a very voluptuous woman with a soft looking afro. Dean spares a thought to Cas’s flexibility with inviting partners into bed, but then she quickly dismisses it. They aren’t even dating yet.

Dean’s next two dates are bland. She tries to engage number nine because she’s actually super sweet, but Cas is in the forefront of Dean’s mind, and Emily didn’t have a chance. Dean hopes Emily’s last date is a good one to make up for their shitty one. Date ten is okay, but Dean has no qualms about not being invested. David had met someone else already, too. 

When the final bell sounds, Dean doesn’t bother to get into the line forming to give the organizer her date card. She looks to catch up with Miranda to let her know that she found someone else. Miranda takes the news well, and, though disappointed, she claims to be happy for Dean before shooing her off.  


Dean next finds Cas, and she make her way to him, a grin on her face.

“Heya, handsome.”

Cas smiles while he stands to greet her. “Hello, Dean. You seem eager to see me again.”

“Shut up.” Dean gives him a light shove. “We both knew I wasn’t gonna turn my card in and come find you.”

“I didn’t, actually.”

“I’m pretty sure I heavily implied that when I said we’d be meeting up afterwards. You aren't in line either.”

“Of course you did. And it's easier to wait it out sitting.”

Dean fits her hand into Cas’s. “I did. And sure that's why.”

“Uh huh.” Cas steps closer to her, putting them almost into kissing range. “So how were your last dates?”

“They had no chance. You?”

“Same. Though Vera was very engaging.”

“Was she the one with the afro?”

“Mhm. Were you watching me?”

Dean blows breath onto Cas’s face and feels satisfaction when Cas simply blinks at her. “Just for a moment.”

“Now who’s jealous?”

“I wouldn’t say that. More turned on than anything.”

Cas’s eyebrows furrow. “Why?”

“You're both hot, Cas. You’re a big boy. Put the pieces together.”

“I’m at a loss.”

Dean swallows, takes the plunge. “You’d look good having sex together.”

“Is watching something you enjoy?”

“Sometimes.”

Cas tilts his head and swings their arms. “Mm.”

“Mm.”

“Mm.” Cas smiles wide.

“You fucker, I’m not doing this all night.”

“Mhm.”

“Shut up.”

“I think the appropriate phrase here is make me?”

Dean raises an eyebrow. “If I make you, we’re definitely not gonna stay PG-13.”

“We can’t have that, can we? It’ll be a scandal.”

Dean snickers. “Maybe not for the bar, but definitely some of the people here.”

Cas pulls Dean closer, and he leans his forehead onto Dean’s. Dean lets her free hand go to Cas’s waist. The smile on Cas’s face turns tender, and Dean notices that his eyes really crinkle while she lets her lips form a smile in return. She watches as Cas closes his eyes and spares a thought that things are evolving way too fast. 

They stand there for a while, ignoring the rest of the daters milling about. Dean catches Benny’s eye over Cas’s shoulder at one point, and she glares when he all too happily nods at Cas. Whatever. He doesn’t have to be smug about having urged Dean to go back. She quickly looks back at Cas, his eyes still closed and all to content to just rest with Dean. He’d be good in bed just for cuddling, Dean thinks.  


A tap to the shoulder brings Dean back into reality. She turns her head, jostling Cas, and looks at who’s trying for her attention. It’s Gilda. 

“Sorry to interrupt, but I’d like to go home now?”

Cas opens his eyes and shots Dean a confused look. Dean rubs Cas’s waist with her fingers. 

“I’m Gilda’s ride. She’s the one who suckered me into this.”

Cas nods and turns to Gilda. “Thank you for that.”

“No problem.” A hesitant smile at Dean. “I told you so.”

“Yeah, yeah. Going out was good for me and all that.”

“So we can go now?”

Dean shakes her head. She removes her hand from Cas’s waist and digs her phone out of her pocket. Cas takes it from her fingers to put his number in. He slips it back in Dean’s pocket himself, and he smiles at Dean’s startled noise. 

“I think you can go now, Dean.”

Dean narrows her eyes for only a moment before mumbling _a see you later_. Cas simply lets his grin stay on his face and watches the two women leave. 


End file.
